7-Hydroxy-5,6-dihydro-4H-dibenzo[de,h]quinoline → 7-Hydroxy-5,6,8,9,10,11-hexahydro-4H-dibenzo[de,h]-quinoline

HRID 65693Notes

Reaction equation

HRID 65693 reaction equation
[OH:1][C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[C:5]3[CH2:16][CH2:17][CH2:18][C:3]=1[C:4]=23>C(O)(=O)C.[Pt]>[OH:1][C:2]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[C:5]3[CH2:16][CH2:17][CH2:18][C:3]=1[C:4]=23

Participants

4

Reactant 1

HCID 120709657-Hydroxy-5,6-dihydro-4H-dibenzo[de,h]quinoline

Product 1

HCID 216719417-Hydroxy-5,6,8,9,10,11-hexahydro-4H-dibenzo[de,h]-quinolineYield 86.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

7-Hydroxy-5,6-dihydro-4H-dibenzo[de,h]quinoline (16.4 g) and Adams platinum (2.78 g) suspended in acetic acid (400 cc) are placed under an initial hydrogen pressure of 25 bars at 25° C. The mixture is stirred and heated at 65° C. for 24 hours. After cooling to 25° C., the catalyst is filtered off and washed three times with acetic acid (total 200 cc). The combined organic filtrates are evaporated to dryness. The residue is taken up in water (500 cc) and the mixture is neutralised by the addition of a 10% (w/v) aqueous sodium bicarbonate solution (50 cc). The precipitate is filtered off, washed three times with distilled water (total 600 cc) and dried under reduced pressure. The crystalline product thus obtained (17 g) is combined with a portion (7.4 g) of product prepared in the same way, the whole is recrystallised from butyl acetate (550 cc). After cooling for 48 hours at about 5° C., the resulting crystals are filtered off, washed twice with diethyl ether (total 75 cc) and dried under reduced pressure (1 mm Hg) at 100° C. The product obtained (18.5 g) is recrystallised a second time from propanol (360 cc). After cooling for 48 hours at about 5° C., the crystals are filtered off, washed twice with diethyl ether (total 75 cc) and dried under reduced pressure (1 mm Hg) at 100° C. for 4 hours. 7-Hydroxy-5,6,8,9,10,11-hexahydro-4H-dibenzo[de,h]-quinoline (14.5 g), melting at 224° C., is thus obtained.

Workup

  1. customat 25° C
  2. temperatureAfter cooling to 25° C.
  3. filtrationthe catalyst is filtered off
  4. washwashed three times with acetic acid (total 200 cc)
  5. customThe combined organic filtrates are evaporated to dryness
  6. additionthe mixture is neutralised by the addition of a 10% (w/v) aqueous sodium bicarbonate solution (50 cc)
  7. filtrationThe precipitate is filtered off
  8. washwashed three times with distilled water (total 600 cc)
  9. customdried under reduced pressure
  10. customThe crystalline product thus obtained (17 g)
  11. customprepared in the same way
  12. customthe whole is recrystallised from butyl acetate (550 cc)
  13. temperatureAfter cooling for 48 hours at about 5° C.
  14. filtrationthe resulting crystals are filtered off
  15. washwashed twice with diethyl ether (total 75 cc)
  16. customdried under reduced pressure (1 mm Hg) at 100° C
  17. customThe product obtained (18.5 g)
  18. customis recrystallised a second time from propanol (360 cc)
  19. temperatureAfter cooling for 48 hours at about 5° C.
  20. filtrationthe crystals are filtered off
  21. washwashed twice with diethyl ether (total 75 cc)
  22. customdried under reduced pressure (1 mm Hg) at 100° C. for 4 hours

Sources & evidence

ORD record
ord-9f587fda73dd47179957c4d0f45499ab
Source dataset
uspto-grants-1978_12
Patent number
US04128650

Reaction notes

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